3553. Elymoclavine

Nomenclature

CAS number: 548-43-6
8,9-Didehydro-6-methylergoline-8-methanol.
C16H18N2O; mol wt 254.33.
C 75.56%, H 7.13%, N 11.01%, O 6.29%.

Description and references

An ergot alkaloid obtained from cultures of fungi parasitic on Elymus mollis Trin.: Abe et al., US 2835675 (1958). Found in fungi parasitic on Pennisetum typhoideum Rich.: Stoll et al., Helv. Chim. Acta 37, 1815 (1954). Structure and stereochemistry: Schreier, Helv. Chim. Acta 41, 1984 (1958). Biosyntheses utilizing Claviceps cultures: Naidoo et al., Chem. Commun. 1970, 472; Ogunlana et al., ibid. 775; Seiler et al., ibid. 1394; Cavender, Anderson, Biochim. Biophys. Acta 208, 345 (1970).

Chemical structure

Properties

Monoclinic prisms from methanol, 248-252° (dec). [α]D20 -59° (c = 0.1 in ethanol) (Abe); [α]D20 -152° (c = 0.9 in pyridine) (Stoll). uv max: 227, 283, 293 nm (log ε 4.31, 3.84, 3.76). Fairly sol in water with alkaline reaction. Sol in pyridine; very slightly sol in organic solvents.